Nate Cooper (Joel David Moore) has never gotten over his first crush from elementary school, Cristabelle (Paris Hilton). Now in his 20s, Nate meets Cristabelle on a Los Angeles beach. His love hasn't waned, and he vows to date her. Unfortunately, the beautiful Cristabelle will not date anyone unless her severely ugly friend, June (Christine Lakin), has a date as well. But, when June gets a complete makeover, Nate begins to realize he might actually be in love with her.